An efficient and expeditious synthesis of di- and monosubstituted 2-aminoimidazoles

被引:25
作者
Soh, Chai Hoon [1 ]
Chui, Wai Keung [2 ]
Lam, Yulin [1 ]
机构
[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
[2] Natl Univ Singapore, Dept Pharm, Singapore 117543, Singapore
来源
JOURNAL OF COMBINATORIAL CHEMISTRY | 2008年 / 10卷 / 01期
关键词
D O I
10.1021/cc700143n
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A microwave-assisted protocol was developed for the construction of di- and monosubstituted 2-aminoimidazoles. The two-step reaction involves the synthesis of N-(1H-imidazol-2-yl)acetamides from readily available alpha-haloketones and N-acetylguanidine, followed by deacetylation. Significant rate enhancement was observed for both steps of the protocol, and the overall reaction time was shortened to 20 min compared to 48 h of the conventional procedures. A representative set of di- and monosubstituted 2-aminoimidazoles was prepared using commercially available parallel reactors.
引用
收藏
页码:118 / 122
页数:5
相关论文
共 50 条
[31]   An efficient stereocontrolled synthesis of di- and triunsaturated carbonyl compounds [J].
Mladenova, M ;
Alami, M ;
Linstrumelle, G .
SYNTHETIC COMMUNICATIONS, 1996, 26 (15) :2831-2842
[33]   A three-component, Zn(OTf)2-mediated entry into trisubstituted 2-aminoimidazoles [J].
Lukin, Alexei ;
Bakholdina, Anna ;
Kryukova, Anna ;
Sapegin, Alexander ;
Krasavin, Mikhail .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2019, 15 :1061-1064
[34]   Identification of aryl 2-aminoimidazoles as biofilm inhibitors in Gram-negative bacteria [J].
Bunders, Cynthia A. ;
Richards, Justin J. ;
Melander, Christian .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (12) :3797-3800
[35]   Synthesis of Substituted 2-Aminoimidazoles via Pd-Catalyzed Alkyne Carboannination Reactions. Application to the Synthesis of Preclathridine Natural Products [J].
Zavesky, Blane P. ;
Babij, Nicholas R. ;
Wolfe, John P. .
ORGANIC LETTERS, 2014, 16 (18) :4952-4955
[36]   A multicomponent reaction of 2-aminoimidazoles: microwave-assisted synthesis of novel 5-aza-7-deaza-adenines [J].
Lim, Felicia Phei Lin ;
Low, Szy Teng ;
Ho, Elvina Lee King ;
Halcovitch, Nathan R. ;
Tiekink, Edward R. T. ;
Dolzhenko, Anton V. .
RSC ADVANCES, 2017, 7 (81) :51062-51068
[37]   2-aminoimidazoles collapse mycobacterial proton motive force and block the electron transport chain [J].
Albert Byungyun Jeon ;
David F. Ackart ;
Wei Li ;
Mary Jackson ;
Roberta J. Melander ;
Christian Melander ;
Robert B. Abramovitch ;
Adam J. Chicco ;
Randall J. Basaraba ;
Andrés Obregón-Henao .
Scientific Reports, 9
[38]   2-aminoimidazoles as guanidine mimetics in a series of potent, selective isoxazoline αvβ3 antagonists [J].
Wityak, J ;
Pitts, WJ ;
Tobin, AE ;
Estrella, MJ ;
Harlow, PP ;
Corjay, MH ;
Mousa, SA ;
Wexler, RR ;
Jadhav, PK .
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 215 :U886-U886
[39]   A new efficient synthesis of long-chain di- and triaminopolyols [J].
Coste, Gerald ;
Gerber-Lemaire, Sandrine .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (17) :3903-3909
[40]   SYNTHESIS OF DI- AND TRIALKYLAZULENES [J].
PAI, BR ;
SANTHANA.PS ;
SRINIVAS.M .
TETRAHEDRON, 1966, 22 (10) :3417-&